2-(Trimethylsilyl)ethanol

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethanol
• CAS No.: 2916-68-9
• Molecular Formula: C5H14OSi
• Molecular Weight: 118.251
• Hs Code.: 29310095
• European Community (EC) Number: 220-844-5
• NSC Number: 96784
• UNII: GF24TDM0VO
• DSSTox Substance ID: DTXSID80183421
• Nikkaji Number: J49.849A
• Wikidata: Q72514447
• ChEMBL ID: CHEMBL25482
• Mol file: 2916-68-9.mol

Synonyms:2-(trimethylsilyl)ethanol;2-TMSE

Chemical Property of 2-(Trimethylsilyl)ethanol

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 1.972mmHg at 25°C
• Melting Point: 0oC
• Refractive Index: n20/D 1.423(lit.)
• Boiling Point: 144.962 °C at 760 mmHg
• PKA: 15.38±0.10(Predicted)
• Flash Point: 50.556 °C
• PSA: 20.23000
• Density: 0.819/cm³
• LogP: 1.31690
• Storage Temp.: 0-6°C
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 118.081391600
• Heavy Atom Count: 7
• Complexity: 46.5

Purity/Quality:

99% ^*data from raw suppliers

2-(Trimethylsilyl)ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-37/39-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CCO
• Physical properties: bp 50–52 °C/10 mmHg, 71–73 °C/35 mmHg; d 0.825 g cm?3.
• Uses: 2-(Trimethylsilyl)ethanol is used as a protecting reagent for carboxyl, phosphoryl, hydroxyl and amino group in organic synthesis. It is used as a precursor to prepare trimethyl(2-phenoxyethyl)silanes by reacting with aromatic fluoride. It is also used in the synthesis of teoc-protected amines by using the corresponding isocyanates. Used to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates. 2-(Trimethylsilyl)ethanol is a protecting reagent for carboxyl, phosphoryl, hydroxyl, and amino groups. It participates in the reactions of Phenol and Acid Protection, Alcohol Protection, Hemiacetal Protection, Amine Protection, Enol Ether Synthesis, Carbohydrate Chemistry etc.

Technology Process of 2-(Trimethylsilyl)ethanol

There total 16 articles about 2-(Trimethylsilyl)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

B-<2-(trimethylsilyl)ethyl>9-borabicyclo<3.3.1>nonane (72610-05-0) → 2-(Trimethylsilyl)ethanol (2916-68-9) + cis-1,5-cyclooctanediol (23418-82-8)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In water; for 1h; Heating;

DOI:10.1021/jo01306a006

Reference yield: 98.0%

Trimethylsilanyl-(2,8,9-trioxa-5-aza-1-germa-bicyclo[3.3.3]undec-1-yl)-acetic acid methyl ester → 2-(Trimethylsilyl)ethanol (2916-68-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 16h; Ambient temperature;

DOI:10.1002/cber.19971300611

Reference yield: 88.0%

ethenyltrimethylsilane (754-05-2) → (+-)-1-(trimethylsilyl)ethanol (13246-39-4) + 2-(Trimethylsilyl)ethanol (2916-68-9)

Guidance literature:

With oxonium; oxygen; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; Product distribution; regioselectivity of hydroalumination;

upstream raw materials:

2,2-dimethyl-propanoic acid ethyl ester

methyl (trimethylsilyl)acetate

formaldehyd

(trimethylsilyl)methylmagnesium chloride

Downstream raw materials:

2-(trimethylsilyl)ethyl acetate

7-Oxo-octansaeure-(2-trimethylsilyl-ethylester)

carbamic acid 2-trimethylsilylethyl ester

2-(trimethylsilyl)ethyl chloride

Refernces

Synthesis of monocrotaline by nucleophilic macrolactonization

10.1021/jo00226a045

The research focuses on the synthesis of monocrotaline, a macrocyclic dilactone pyrrolizidine alkaloid, which is notable for its potent hepatotoxic and antitumor activity, as well as its role as a defensive agent and pheromone precursor in Danaid butterflies. The study addresses the challenges in synthesizing the 11-membered derivative monocrotaline, particularly its tendency for y-lactone formation, which complicates synthetic strategies. The researchers developed a sequence involving the coupling of compounds 10 and 6, followed by nucleophilic ring closure, which includes the displacement of mesylate by a carboxylate ion generated in situ through the desilylation of a β-(trimethylsilyl)ethyl ester 3. Key chemicals used in the process include retronecine derivatives, glutaric anhydride derivative 5, 2-(trimethylsilyl)ethanol, and various reagents for cyclization and deprotection steps. The conclusions of the research confirm the generality of the nucleophilic cyclization method for the synthesis of retronecine-derived dilactones and provide a complete synthesis of monocrotaline, highlighting the effectiveness of the method in the case of pyrrolizidine alkaloids.